Acetic Acid → 5-Chloro-2-hydroxy-3-methoxybenzaldehyde

HRID 1910649

Reaction equation

HRID 1910649 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].C(O)(=O)C.[Cl:16]N1C(=O)CCC1=O>O>[Cl:16][C:10]1[CH:9]=[C:6]([O:7][CH3:8])[C:4]([OH:5])=[C:3]([CH:11]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8991o-VanillinHCID 31398Chlorosuccinimide

Product 1

HCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehydeYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

o-Vanillin (100.5 g, 660 mmol), acetic acid (504 mL) and N-chlorosuccinimide (83.8 g, 627 mmol) were mixed and heated to 105° C. over 30 minutes. A rapid exotherm from 55 to 105° C. occurred over 7 minutes. The mixture refluxed for a few minutes and was allowed to cool slowly to room temperature (2.5 h). Water (1 L, 2 volume equivalents) was added to the mixture slowly over 10 minutes. The mixture was stirred for 5 minutes, filtered and the crude product air dried to afford 146.9 g of wet cake as a light yellow powder with 90% product, 3% o-vanillin and 7% dichlorovanillin Recrystallization from 200 g ethanol afforded 61 g (52% yield).

Workup

  1. temperatureThe mixture refluxed for a few minutes
  2. temperatureto cool slowly to room temperature (2.5 h)
  3. filtrationfiltered
  4. dry with materialthe crude product air dried
  5. customto afford 146.9 g of wet cake as a light yellow powder
  6. customwith 90% product, 3% o-vanillin and 7% dichlorovanillin Recrystallization from 200 g ethanol
  7. customafforded 61 g (52% yield)

Sources & evidence

ORD record
ord-0eff40f3de234f0e9aabd1b5ed6deb1d
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Linked notes

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